FR3035659A1 - USE OF A COMPOSITION COMPRISING A C7-C15 MONO- TO TETRA-ALKYLENATE OF MONO- TO TETRA- (C3-C6 TRIALKANOL) AS AN AUXILIARY FOR THE IMPLEMENTATION OF BITUMINOUS PRODUCTS AND / OR CONCRETE - Google Patents

Abstract

The present invention relates to the use of a composition comprising a mono- to tetraalkylenate C7-C15 mono- to tetra- (trialkanol C3-C6) as an auxiliary implementation of bituminous products and / or concrete .

Description

Use of a composition comprising a mono- to tetraalkylenate C7-C15 mono- to tetra- (trialkanol C3-C6) as an auxiliary implementation of bituminous products and / or concrete The present invention relates to a composition comprising a processing aid for bituminous products and / or concrete. More particularly, it relates to a composition comprising a mono- to tetraalkylene C7-C15 mono- to tetra (trialkanol C3-C6) as an auxiliary implementation of bituminous products and / or concrete. The construction of civil engineering works and the laying of various coatings on these structures must meet many requirements, particularly in terms of quality.

The use of concrete and / or bituminous products is therefore very important and must be mastered optimally. There are currently many agents to facilitate the application of the concrete and / or to increase the durability of the concrete. By way of example, mention may be made of curing agents which are intended to protect the concrete against too rapid evaporation of water during its installation, especially when the climatic conditions are severe (for example: wind, sun, low humidity). Indeed, it has been shown that too rapid evaporation of water in the concrete was responsible for the formation of defects and thus a decrease in the durability of the concrete. The commonly used curing agents have a petrochemical origin and leave a residue on the cured surface thus requiring a cleaning step. When making concrete structures, mold release agents are also used which make it possible, during demoulding, to separate the hardened concrete from its mold, called formwork. Stripping is an operation that gives the desired shape and appearance to the concrete. In the absence of an interface between the concrete and the formwork, bonding is inevitable with a high risk of destruction of the two surfaces at demolding. A mold release agent has several roles: in addition to facilitating the separation of concrete and mold, it protects the formwork from corrosion if it is made of steel and improves the surface appearance of the concrete. Among the various types of demolding agents that exist (formwork, chemical agents, etc.), the most used today are oil emulsions, waxes or mineral, synthetic or vegetable oils. The advantage of these agents is to respect the integrity of the formwork and to promote a smooth-looking concrete surface. However, they have some disadvantages such as the possibility of clogging of the formwork. In addition, these agents leave on the surface of the demolded part a dusty veil. Moreover, the application of bituminous products poses many problems of fouling tools. Thus, it is common to apply a release agent on the metal or plastic surfaces (rubber for example) that are in contact with the bituminous products during transport or laying, for example, so that the bituminous products do not adhere to said surfaces. Commonly, for this purpose, we used diesel. However, the diesel has been classified CMR and its use for this purpose is prohibited.

Various esters were then used as anti-adherents. However, these also have flow rate properties, that is to say, they dissolve the bitumen, which cause problems when applying the bitumen.

2 3035659 Thus, it would be interesting to have an auxiliary to facilitate the implementation of bituminous products and / or concrete. However, the inventors have demonstrated that the use of a mono- to tetraalkylene-C7-C15 mono- to tetra (C3-C6 trialkanol) allowed to meet these requirements. Thus, a first object of the invention is the use of a composition comprising a mono- to tetraalkylene C7-C15 mono- to tetra- (C3-C6 trialkanol) as an auxiliary for the implementation of bituminous and / or concrete products. According to the invention, "auxiliary processing" means an agent for improving the application of concrete and / or bituminous products, that is to say, to facilitate the implementation and / or to improve the properties of the product 15 thus implemented (particularly aesthetic, mechanical performance of concrete), while protecting the implementation devices. According to the invention, "bituminous products" means a product comprising a mixture of hydrocarbons with possibly other adjuvants. According to one embodiment, the bituminous product is a material whose binder is bitumen. Examples include hot mixes, cold mixes, severe emulsions or asphalt.

According to the invention, "concrete" means a mixture comprising water (E), cement (C) having an E / C ratio of between 0.2 and 0.8; preferably between 0.3 and 0.7 and aggregates. The concrete may also comprise adjuvants such as retarders or setting accelerators, air entraining devices, pigments, air reducers, viscosifiers or plasticizers and water-reducing superplasticizers.

According to one embodiment, the concrete is chosen from the concretes mentioned in standard NF EN 206-1. For example, concrete of resistance class B20 / 25 commonly used in the building.

According to one embodiment, the C7-C15 mono- to tetraalkylene alkyl of C3-C6 mono- to tetra (trialkanol) is selected from the group consisting of mono- to tetra-esters of the formula CH2 = CH (CH2) nCOOH with n being 4, 5, 6, 7, 8, 9, 10, 11 or 12 with mono- to tetra- (C3-C6 trialkanol), preferably glycerol. According to a particular embodiment, the C7-C15 mono- to tetraalkylene alkyl of mono- to tetra (C3-C6 trialkanol) is selected from the group consisting of glycerol monoundecylenate, glycerol di-undecylenate, glycerol tri-undecylenate, glycerol mono-nonylenate, diglycerol mono-undecylenate, diglycerol di-undecylenate, diglycerol tri-undecylenate, diglycerol tetra-undecylenate and mixtures thereof. Particularly advantageously, the mono- to tetra C7-C15 alkylenate of mono- to tetra- (C3-C6 trialkanol) is a biobased product. In particular, it is possible to use a mixture of glycerol mono-undecylenate, glycerol di-undecylenate and glycerol tri-undecylenate, hereinafter referred to as MUG, or a mixture of diglyceryl mono-undecylenate, diglyceryl-diecylenate diglycerol tri - undecylenate and diglycerol tetra - undecylenate, hereinafter referred to as MUDG. The MUG or DUG may also include undecylenic acid. According to one embodiment, the MUG comprises: 0 to 90%, preferably 20 to 80%, and even more preferably 55 to 70% molar of glycerol monoundecylenate, 0 to 90% %, even more undecylenate from 0 to 50%, even more undecylenate preferably from 0 to 50%, and preferably from 20 to 30 mol% of di-glycerol; preferably from 0 to 10%, and preferably from 0.5 to 5 mol% of tri-glycerol; at least one being present. According to a particular embodiment, the MUG 10 comprises: 66 mol% of glycerol mono-undecylenate 26 mol% of glycerol di-undecylenate 0.9 mol% of glycerol tri-undecylenate; and 6.9 mol% of undecylenic acid.

According to one embodiment, the MUDG comprises: 0 to 90%, preferably 20 to 80%, and even more preferably 55 to 70 mol% of diglycerol mono- undecylenate, 0 to 90% preferably from 0 to 50%, and even more preferably from 20 to 30 mol% of diglycerol diundecylenate; from 0 to 50%, preferably from 0 to 10%, and even more preferably from 0.5 to 5 mol% of diglycerol tri-undecylenate; from 0 to 50%, preferably from 0 to 10%, and even more preferably from 0.2 to 5 mol% of diglycerol tetraundecylenate, at least one being present.

According to a particular embodiment, the MUDG comprises: 64.15 mol% of diglycerol mono-undecylenate 24.9 mol% of diglycerol di-undecylenate 4.4 mol% of diglycerol tri-undecylenate; 0.21 mol% of diglycerol tetra-undecylenate, and 6.35 mol% of undecylenic acid.

The mono- to C7-C15 tetraalkylenate of mono- to tetra (C3-C6) trialkanol can be obtained by the following method: (a) Mixing of the alkyleneic acid with a C3-C6 trialkanol, (b) Heating the mixture obtained in step (a) to a temperature between 30 and 180 ° C, preferably between 100 ° C and 140 ° C and even more preferably at 80 ° C. (c) adding dodecylbenzene sulfonic acid and a water scavenger to the mixture of step (b); (d) mixing for a time sufficient for the reaction to take place, typically between 30 minutes and 6 hours, preferably 1 hour; (e) cooling the mixture of step (d); and (f) separating the organic phase and the aqueous phase to obtain C7-C15 mono- to tetraalkylenate of mono- to tetra (C3-C6 trialkanol) contained in the organic phase. This process is particularly advantageous because it allows a good regioselectivity of the esterification reaction.

MUG and MUDG can be obtained according to the following process: (a) Mixing of undecylenic acid with glycerol (for the preparation of the MUG) or with diglycerol (for the preparation of MUDG), (b) Heating the mixture obtained in step (a) at a temperature between 30 and 180 ° C, preferably between 100 ° C and 140 ° C and even more preferably at 80 ° C, (c) Addition of dodecylbenzene acid sulfonic acid and a water scavenger to the mixture of step (b); (D) mixing for a time sufficient for the reaction to take place, typically between 30 minutes and 6 hours, preferably 1 hour; (e) cooling the mixture of step (d); and (f) Separation of the organic phase and the aqueous phase to obtain the MUG or MUDG contained in the organic phase. Mold Release Agent According to one embodiment, the composition is used as a concrete release agent. Indeed, it has been demonstrated by the inventors, by means of experimental data, that a composition comprising a C7-C15 mono- to tetraalkylenate of mono- to tetra (C3-C6) trialkanol makes it possible not only to facilitate the demolding of concrete poured into formwork but also to give a good appearance to the concrete after demolding the formwork leaving no dusty layer on the exposed surface.

Thus, according to one embodiment, the composition is applied to the internal formwork walls before the concrete is poured into said formwork. According to one embodiment, the composition is applied to the internal walls of a horizontal formwork or in a vertical formwork. However, the composition is entirely suitable for use on the internal walls of a vertical formwork for making walls, for example, whose faces will be visible on both sides after stripping.

The composition may be applied to the internal surfaces of the formwork manually by spraying, for example, or mechanically by roller or brush application.

According to one embodiment, the release agent is applied to the internal walls of a formwork at a content of 5 g / m 2 to 50 g / m 2, preferably from 10 g / m 2 to 30 g / m 2. The composition can be applied in excess. In this case, it will be followed by wiping with a cloth or a squeegee, for example. When the composition is used as a release agent, it is in the form of an emulsion further comprising water and vegetable oil. According to one embodiment, the composition comprises: 2-20% by weight, preferably 2-10%, and even more preferably 3-6% of a C7-C15 mono- to C7-C15 tetraalkylenate; to C3-C6 tetra (trialkanol); 15 - 0-90% by weight, preferably 20-85%, and even more preferably 50-80% water - 0-70% by weight, preferably 5-50%, and more preferably 10- 40% vegetable oil.

In one embodiment, the vegetable oil may be a seed or fruit oil. According to one embodiment, it is selected from the group consisting of rapeseed oil, sunflower oil, peanut oil, linseed oil, crambe oil, coconut oil, jatropha and their mixtures. According to a particular embodiment, the vegetable oil is rapeseed oil. In one embodiment, the emulsion further comprises at least one adjuvant selected from the group consisting of a surfactant and an anionic or nonionic antioxidant. According to a particular embodiment, the composition comprises: 2-20% by weight, preferably 2-10%, and even more preferably 3-6% of MUG and / or MUDG; 0-90% by weight, preferably 20-85%, and even more preferably 50-80% water 0-70% by weight, preferably 5-50%, and more preferably 10-50% by weight. 40% vegetable oil.

It has also been demonstrated that a mono- to tetraalkylene C7-C15 mono-tetra (C3-C6 trialkanol) stabilizes an oil-in-water emulsion. Thus, another object of the present invention is an oil-in-water emulsion stabilized with 2 to 20%, preferably 2 to 10%, of a C7-C15 mono- to tetraalkylene mono-tetra- (C3-C6 trialkanol). According to one embodiment, the C7-C15 mono- to tetraalkylene alkyl of C3-C6 mono- to tetra (trialkanol) is MUG or MUDG. Another object of the present invention is the use of a mono- to tetraalkylene C7-C15 alkano to tetra (C3-C6 trialkanol) to stabilize an oil-in-water emulsion.

According to one embodiment, the C7-C15 mono- to tetraalkylene alkyl of C3-C6 mono- to tetra (trialkanol) is MUG or MUDG. Concrete curing agent According to another embodiment, the composition is used as a curing agent for concrete. Indeed, the inventors have demonstrated, through experimental data, that a composition comprising a mono- to tetraalkylenate C7-C15 mono- to tetra- (trialkanol C3-C6) allowed to control the loss of water when drying concrete and thus avoid cracking concrete caused by its removal. The composition also makes it possible to avoid cracking and to avoid the disorganization of the concrete at a young age by allowing the normal development of hydrates. According to one embodiment, the composition is applied to concrete poured into a support.

According to the invention, the composition can be applied to concrete cast on a horizontal support or on a vertical support. However, the composition is entirely suitable for use on concrete cast on a horizontal support because the exchanges with the air are important, thus increasing the risks of too rapid evaporation of the water in the concrete. According to the invention, the composition is applied after the concrete has been poured onto the support. Those skilled in the art will be able to find the time interval between the pouring of the concrete and the application of the composition according to various parameters such as the composition, the rheology of the concrete, its exposure or the weather conditions. By way of example, mention may be made of a time interval between the pouring of the concrete and the application of the composition between 1 and 3 hours for a concrete of the B20 / 25 type and of consistency class S2. According to one embodiment, the composition is applied to the concrete at a content of 40 to 750 g / m 2, preferably from 50 g / m 2 to 400 g / m 2, and even more preferably from 100 g / m 2 to 300 g / m 2 . The application can be done by spraying. The curing agent described above is suitable for all types of concrete, in particular concretes having an E / C ratio between the quantity of water and the quantity of cement ranging from 0.3 to 0.6, of preferably from 0.25 to 0.50.

In another embodiment, the composition is used as an anti-adherent agent for bituminous products.

Indeed, it has been demonstrated by the inventors that a composition comprising a C7-C18 mono- to tetraalkylene alkyl of C3-C6 mono- to tetra- (trialkanol) allowed surfaces to not adhere to bituminous products when the latter were in contact with said bituminous products. According to one embodiment, the composition is applied to metal surfaces and / or plastic surfaces. The application can be done by spraying. In particular, the composition is applied to bituminous product spreading screws, handle tools, boots, etc. Particularly advantageously, because of its high adsorbance, the application on the metal surfaces does not have to be repeated before each contact of the metal surface with the bituminous product, but may allow the use of the tools during several cycles of use without renewal of the application. The application of the composition does not cause the dissolution of the bitumen contained in the bituminous material.

According to the invention, when the composition is used as a concrete curing agent or as a release agent for bituminous products, the composition is an aqueous solution whose concentration of mono- to tetraalkylene C7-C15 mono- to tetra (C 3 -C 6 trialkanol) is between 5% and 65%, preferably between 15% and 50%, preferably between 20% and 30%. According to one embodiment, the aqueous solution further comprises at least less an adjuvant selected from the group consisting of surfactants or short chain esters in small amounts.

According to one particular embodiment, the composition is an aqueous solution whose concentration of MUG and / or MUDG is between 5% and 65%, preferably between 15% and 50%, preferably between 20% and 30%. .

FIGS. 1a-1c show the appearance of stainless steel plates previously protected by a MUG non-stick composition (FIG. 1a), MUDG (FIG. 1b) and comparative compositions (FIG. 1c) after sliding a loaf. asphalt.

Figure 2a shows the values of the protection coefficient obtained for different compositions (at t = 6h and t = 24h). Fig. 2b is a graph illustrating the protection coefficient obtained at 24 h with a MUG based on (a) the amount of product reduced to m 2 and (b) the MUG assay in the% preparation. Figure 2c is a graph illustrating the protection coefficient (at 6h and 24h) as a function of the amount of MUG reduced per m2 of surface treated.

Fig. 3 shows the appearance of a molded plate with a vegetable oil composition (Fig. 3a) and with a composition comprising MUDG (Fig. 3b). Figures 4 are microscopic views before centrifugation of emulsions (stabilized with MUDG, stabilized with MUG, commercial emulsion (top to bottom)) and the appearance of specimens after centrifugation (3000 RPM). EXAMPLES Example 1: Preparation of the MUG and MUDG Preparation of the MUG: The MUG is obtained according to the following operating protocol: Glycerol (98%, 8 kg) and undecylenic acid (99%, 8 kg) 12 3035659 are introduced in a 25 L jacketed batch reactor equipped with a coolant, a dean-stark and a mechanical stirrer (500 rpm). The reactor is heated to 120 ° C. Then dodecylbenzene sulfonic acid (97%, 1.78 kg) and molecular sieve 3 (1.2 kg) are introduced. The reaction time is taken as soon as the dodecylbenzene sulphonic acid is introduced. The duration of the reaction is lh. After one hour of reaction, the reaction mixture is analyzed by gas chromatography (GC) and infrared spectroscopy (IRTF). The reaction mixture is cooled to 60 ° C. The organic phase is first transferred to a 20 L can with a funnel equipped with a strainer to remove the molecular sieve and then in a 30L decanter. The organic phase is washed with 3 × 20L of saturated NaCl water solution. The separation of the organic phase and the aqueous phase is by decantation. The conversion to undecylenic acid is 69.4% and the yield of the reaction in mono-undecylenate of glycerol is 56.8%. The water content of the final reaction medium is 22%. The molar composition of the final product is: glycerol mono-undecylenate: 66% glycerol di-undecylenate: 26% glycerol tri-undecylenate: 0.9% undecylenic acid: 6.9% Preparation of MUDG: MUDG is obtained according to the following operating procedure: The linear diglycerol (98%, 508.4 g) and the undecylenic acid (99%, 281.9 g) are introduced into a 1 L double-jacketed batch reactor equipped with a refrigerant, a dean-stark and a mechanical stirrer (500 rpm). The reactor is heated to 120 ° C. Then dodecylbenzene sulfonic acid (97%, 62.44 g) and molecular sieve 3A (73.8 g) are introduced. The reaction time is taken as soon as the dodecylbenzene sulfonic acid is introduced. The duration of the reaction is lh. After one hour of reaction, the reaction mixture is analyzed by gas chromatography (GC) and infrared spectroscopy (IRTF). The reaction mixture is cooled to 60 ° C. The organic phase is transferred first into a 2L separating funnel. The molecular sieve is recovered in the bottom of the reactor. The organic phase is washed with 4 x 400 ml of a solution of water saturated with NaCl. The separation between the organic phase and the aqueous phase is by decantation. The conversion to undecylenic acid is 73.3% and the yield of the reaction to mono-undecylenate diglycerol is 49.5%. The molar composition of the final product is: diglycerol mono-undecylenate: 64.15% diglyceryl di-undecylenate: 24.9% diglyceryl tri-undecylenate: 4.4% diglycerol tetra-undecylenate: 0.21% Acid Example 2: Use of the composition described in the invention as an anti-adherent for bituminous products Experimental protocol In this example, 20 x 40 cm 2 stainless steel metal plates were sprayed with different compositions (described below). The compositions were sprayed at a level of 20 g / m 2. The plates are thermostatically controlled between 60 and 70 ° C.

Pellets of 1000 ± 10 g hot mix (150 ± 10 ° C) were fed to the horizontally held plates. A 20 kg ballast placed on the slabs makes it possible to obtain a pressure of 2.5 kPa at the slab-plate interface to simulate the transport phase of the mix by truck.

14 3035659 After a one-hour delay and ballast removal, the plates were tilted at a 45 ° angle to simulate the spill phase of asphalt on a road site. The appearance of the plates after pouring the mix was determined for each of the compositions below. - MUG / WATER 5 H 95 H> 5% MUG whose composition and method of obtaining are detailed in Example 1 and 95% water (mass) 10 MUG / WATER MUG / WATER MUG / WATER MUG / WATER MUG / WATER 10 / 90H> 10% of 15 / 85H> 15% of 20 / 80H> 20% of 30 / 70H> 30% of 50/50-f 50% of MUG and MUG and MUG and MUG and MUG and 90% water (mass) 85% water (mass) 80% water (mass) 70% water (mass) 50% water (mass) MUDG / WATER 5/95 H> 5% of MUDG whose composition and the method of obtaining are detailed in Example 1 and 95% water (by weight) MUDG / WATER 10 / 90-10% MUDG / WATER 15 / 85H> 15% MUDG / WATER 20 / 80H> 20% 20 MUDG / WATER 30 / 70H> 30% MUDG / WATER 50/50-F 50% MUDG MUDG MUDG MUDG MUDG & 90% Water & 85% Water & 80% of water and 70% of water and 50% of water (mass) (mass) (mass) (mass) (mass) RD 1 is a formulation comprising diesel, RD 2, and RD 7 are formulations of esters comprising C18: 1 (39-52%) and C18: 2 (24-32%) and RD 4 is a curing product on the market of RIXELLA 415 from Shell®. Results The results are summarized in Table 1 below and the appearance of the plates is illustrated in Figures 30 (compositions comprising MUG), lb (compositions comprising MUDG) and (compositions RD).

15 3035659 Samples Mass residual standard deviation (g / m2) MUG / WATER 5 / 0.08 0.07 95 MUG / WATER 10 / 0.12 0.07 90 MUG / WATER 15 / 0.57 0.26 85 MUG / WATER 20 0.86 0.15 / 80 MUG / WATER 30 0.86 0.24 / 70 MUG / WATER 50 1.41 0.15 / 50 MUDG / WATER 10 0.07 0.05 / 90 MUDG / WATER 15 0.08 0.03 / 85 MUDG / WATER 20 0.10 0.10 / 80 MUDG / WATER 30 0.17 0.06 / 70 MUDG / WATER 50 0.61 0.09 / 50 MUDG 100 1.78 0.08 RD 1 5.25 - * RD 2 5.50 0.13 RD 4 4.39 0.81 RD 7 7.43 0.95 Table 1: Determination of the residual mass of bitumen 16 3035659 Interpretations of the results and conclusions The results above show that the compositions comprising a solution MUDG aqueous or MUG allow to make a metal surface in contact with the bituminous products (here asphalt). Indeed, the residual bitumen mass is less than 1.5 g / m 2 in all compositions comprising MUG or MUDG. It may also be noted that better anti-adherence properties are obtained with highly diluted compositions. In contrast, significant residual masses of asphalt are obtained for the compositions RD1, RD2, RD4 and RD7. These results are consistent with the illustrations of FIGS. 1a-1c which show a significant residual amount on metal plates for compositions RD1, RD2, RD4 and RD7 (FIG. 1c) and a small amount for compositions comprising MUG (FIG. ) or MUDG (Figure lb).

Example 3: Use of the composition described in the invention as a curing agent for concrete The effectiveness of a curing compound is measured by the determination of its protection coefficient. C = [(Pt-Pp) / Pt] * 100 With: 30 Pt = the loss of water of the control sample (thus, unprotected by cure product) in grams Pp = the water loss of the sample protected by the curing product, in grams 17 3035659 values corrected by the loss of clean mass of the cure product in grams The experimental tests were carried out using the NF P18-370 standard but using 45x70x25 test pieces. mm of 160 ± 10 g instead of the prescribed massive test bodies. Experimental protocol - Manufacture of cement paste CEM I 52.5R (Water / Cement ratio of 0.30) - Molding of the paste into wafers 70 × 45 × 25 cm 3 - Vibration of the dough for one minute - Application of the following compositions with small sprays or pipettes: 15 - M75C25CuxMuy (MUG / C11 mixture (25%) / water - diluted to 20% or 50%) - MUGCuxMuy (MUG / water mixture - diluted to 20% or 50%) - Masterkure® 82Cux with x: amount of applied curing agent; Y: amount of MUG applied; and MUG prepared according to Example 1. - Storage of specimens in a room conditioned at 50% RH and 20 ° C. Weighing at regular hours (6h and 24h are important for the calculation of C) - Calculation of the coefficient of protection C given in standard NF P 18-371 Results and conclusions The coefficient of protection obtained with the experimental protocol described leads systematically to lower protection coefficients compared to standard NF P18-370. For example the product Masterkure 82 has a 18 3035659 protection factor at 6h of 82% instead of 90% in standard conditions. The coefficient of protection is even higher when the E / C ratio is low (within the limits of the workability of the cementitious material used) The tests carried out with cement pastes at E / C = 0.3 were shown the most discriminating to qualify the candidate compositions and their positioning in relation to the cure products of the market.

MUG preparations are more effective than MUDG preparations, the latter having greater intrinsic evaporation. As illustrated in FIG. 2a, some of the proposed preparations have exceeded the protection factor of 90% at 6h, especially the formulations formulated with 10% MUG. Given the specific water properties of the MUG, including its capacity for self-organization with variable structure according to its dosage in water, the tests reveal the presence of an optimum around 10%. This optimum would be higher for the MUDG, around 50%. The tests also show that the cure is more effective when the cure product formulated with MUG is applied more abundantly, for example at a rate of 300 g / m2. Commercial products exhibit, on the contrary, a saturation effect beyond 200 to 250 g / m2. The optimum of 10% MUG in water is particularly notable because this small amount leaves little residue on the cementitious material (practically nonexistent). The surfaces, once dry, are therefore able to receive a subsequent treatment (paint or glue). The table below shows the results obtained in terms of protection with the MUG-based preparation.

19 3035659 PROTECTION at 6h IIIIII total quantity of curing compound (test surface -: 30,8cm2) absolute (g) 0.4 0.6 0.9 1.0 1.2 1.5 2.0 2.4 3.0 relative (g / m2) 117 195 292 325 390 487 649 779 974 Cp (MUG / WATER 10%) 97.5% 100.0% 97.3% Cp (MUG / WATER 15%) 100.0% Cp (MUG / WATER 20%) 63.2% 72.4% 84.7% 98.4% 97.5% Cp (MUG / WATER 50%) 52.7 % 65.3% 82.2% 87.2% 90.5% Cp (MK82) 80.5% 82.0% PROTECTION at 24h Total amount of absolute cure (g) 0.4 0.6 0.9 1.0 1.2 1.5 2.0 2.4 3.0 Relative (g / m2) 117 195 292 325 390 487 649 779 974 Cp (MUG / WATER 10%) 85.6% 95.7% 100.0% Cp (MUG / WATER 15%) 95.7% Cp (MUG / WATER 20%) 52.1% 60.1% 75.1% 86.1% 85.6% Cp (MUG / WATER 50%) 44.7% 57.2% 76.3% 85.0% 87.4% Cp (MK82) 79.6% 81.0% Table 2: Influence of the amount applied on the coefficient of protection Table 2 is illustrated in Figure 2a.

The protection criterion is not only the amount of MUG returned to the treated surface, but the torque (cure amount, percent MUG) as shown in Figure 2b.

EXAMPLE 4 Use of the Composition Described in the Invention as a Concrete Release Agent Experimental Protocol Two 40x40x5cm steel molds were cleaned with paper soaked in alcohol.

In the first mold, a composition comprising 35% rapeseed oil and MUG as prepared in Example 1 and 65% water was applied to the walls. In the 2nd mold, a composition of pure vegetable oil rapeseed was applied. Then, B20 / 25 concrete was poured thirty minutes later in each of the molds and demolding was carried out 24 hours later.

Results and Conclusions The slabs thus obtained were observed and are shown in Figures 3a and 3b. Similar results were obtained by replacing the MUDG with MUG.

The application of a composition comprising MUG or MUDG, and preferably MUDG, therefore allows not only easy demolding but also gives a beautiful appearance without whitish deposit on the concrete after demolding (FIG. 3b).

Example 5: Use of the composition described in the invention as a water-in-oil emulsion stabilizer FIG. 4 illustrates the emulsion stabilizing property provided by the MUG and even more so by the MUDG during a test of "Accelerated aging" to break the emulsion using a centrifuge. In the center, the microvoids reveal the smallness of the oil emulsion oil bubbles obtained with MUDG compared to an emulsion on the market (here Rhéofinish® 211). 30 21

Claims (17)

CLAIMS 1-Use of a composition comprising a mono- to tetra-alkylenate at 07-015 of mono- to tetra- (C 3-6 trialkanol) as auxiliary processing of bituminous products and / or concrete. 2-Use according to claim 1, characterized in that the mono- to tetraalkylene C7-C15 alkyl of mono- to tetra- (C3-06 trialkanol) is selected from the group consisting of mono- to tetra-esters of acid of formula CH2 = CH (CH2) nCOOH with n equal to 4, 5, 6, 7, 8, 9, 10, 11 or 12 with a mono- to tetra- (trialkanol at 03-06), preferably glycerol. 3-Use according to claim 1 or 2, characterized in that said C7-C15 mono- to tetraalkylene carbonate of mono- to tetra- (C3-06 trialkanol) is selected from the group consisting of glycerol mono undecylenate , glycerol di - undecylenate, glycerol tri - undecylenate, glycerol mono nonylenate, diglycerol mono - undecylenate, diglycerol di - undecylenate, diglycerol tri - undecylenate, diglycerol tetraundecylenate and mixtures thereof. 4-Use according to any one of claims 1 to 3, characterized in that the composition is used as concrete release agent. 5-Use according to any one of claims 1 to 3, characterized in that the composition is used as curing agent of the concrete. 22 3035659 6-Use according to any one of claims 1 to 3, characterized in that the composition is used as an anti-adherent agent for bituminous products. 7-Use according to claim 4, characterized in that the composition is applied to the internal walls of formwork before the concrete is poured into said formwork. 10 8-Use according to claim 5, characterized in that the composition is applied to cast concrete. 9-Use according to claim 6, characterized in that the composition is applied to a surface, preferably metal, intended to be in contact with a bituminous product. 10- Use according to one of claims 4 or 7, characterized in that the composition is an emulsion 20 further comprising water and vegetable oil. 11. The use as claimed in claim 10, characterized in that the vegetable oil is selected from the group consisting of rapeseed oil, sunflower oil, peanut oil, cranberry oil, coconut oil and the like. linseed oil, jatropha oil and their mixtures. 12- Use according to claim 10, characterized in that the emulsion is stabilized with C7-C15 mono- to tetraalkylenate of mono- to tetra- (C3-C6 trialkanol). 23 3035659 13- Use according to claim 10, characterized in that the emulsion is an oil-in-water emulsion stabilized with 2 to 20% of mono- to tetraalkylene C7-C15 mono- to tetra- (trialkanol C3-06) ). 5 14- Use according to claim 5, 6, 8 or 9, characterized in that the composition is an aqueous solution whose concentration is between 5% and 65%. 10 15. Use according to claim 14, characterized in that the aqueous solution further comprises at least one adjuvant selected from the group consisting of short chain surfactants or esters in small amounts. 16. Use according to one of claims 10 or 11, characterized in that the emulsion further comprises at least one adjuvant selected from the group consisting of a surfactant and an antioxidant. 17. A process for preparing a mono- to tetra (3-trialkanol trialkanol) C 7 -C 15 tetraalkylenate comprising the steps of: (a) Mixing alkyleneic acid with a trialkanol in C3-06, (b) heating the mixture obtained in step (a) to a temperature between 30 and 180 ° C; (c) adding dodecylbenzene sulfonic acid and a water scavenger to the mixture of step (b); (d) mixing for a time sufficient for the reaction to take place, typically between 30 minutes and 6 hours; (e) cooling the mixture of step (d); and (f) Separation of the organic phase and the aqueous phase to obtain C7-C15 mono- to tetraalkylenate of mono- to tetra (C3-C6 trialkanol) contained in the organic phase. 5 25